Chandler, 48, will likely go down as one of the winningest coaches in the history of Winona High School, compiling 87 wins since being named head coach in 2002.
"I'm excited about retiring, but I'm also a little torn," Chandler said. "I love those seventh graders to death, but I knew I probably wouldn't be around to see them play varsity."
Chandler was also named the new head football coach at Winona Christian School, which was confirmed by headmaster Cameron Wright.
Chandler said his excitement is the fact he and his family will get to stay in Winona, as he heads to coach the Stars next season. He said every coach wants to "double dip" and continue coaching in their prime.
Chandler’s reference to double dipping refers to receiving his retirement from public education while continuing to work in the private sector.
"I'm in my prime in coaching, and I'm not too old to coach," Chandler said.
Winona Athletic Director Cole Surrell said Chandler's retirement marks the end of a great career in Tiger athletics.
"He's one of the best coaches to ever come through here," Surrell said. "He has meant a lot to this program."
Chandler said he did not think his retiring had sunk in to many of the players, but he said one thing will remain the same.
"Football will go on for many, many years," Chandler said.
Former Winona standout and Ole Miss defensive back Chief Brown told The Winona Times Tuesday, he was proud to have been coached by Chandler and wished he could have gotten him a championship ring in 2010.
"He [Chandler] gave a lot of players an opportunity to better themselves," Brown said. "For me, I got a chance to play at a Division I school and in the SEC."
According to Wright, who is in his third year as WCS' headmaster, Chandler will serve as both athletic director and head football coach.
Wright said, "I think he'll be good for our school."